Drupal has entered it's 8th cycle. As such, Im regularly asked what I think the top usability issues are. Honestly, this is the first time I've put them down on paper, so this is a bit of a swag, but here it goes...
- Connect the dots. This would be my over-arching theme of Drupal 8. D7 gave us a hint of this where links to configure and permissions were provided in context after enabling a module, but there's so much more to do. One example of this is creating a menu item through the menu itself; you have to know the URL in which you want to link to.